An autonomous Objectively Optimized Observation Direction System (OOODS) is of great utility for NASA's observation and exploration objectives. In particular, to have a fleet of smart assets that can be reconfigured based on the changing needs of science and technology. This proposal describes an OOODS designed as a sensor web element (plug-in) that is of use both now and for future NASA observing systems. The OOODS would integrate a modeling and assimilation system within the sensor web allowing the autonomous scheduling of the chosen assets and the autonomous provision of analyses to users. The OOODS operates on generic principles that could easily be used in configurations other than the specific examples described here. Metrics of what we do not know (state vector uncertainty) are used to define what we need to measure and the required mode, time and location of the observations, i.e. to define in real time the observing system targets. Metrics of how important it is to know this information (information content) are used to assign a priority to each observation. The metrics are passed in real time to the sensor web observation scheduler to implement the observation plan for the next observing cycle. The same system could also be used to reduce the cost and development time in an Observation Sensitivity Simulation Experiment (OSSE) mode for the optimum development of the next generation of space and ground-based observing systems. The entry TRL is 4 the exit TRL is 7.